Your Guide to a Route 66 Road Trip

Get your kicks on America's original road trip—this 2,448-mile journey from Chicago to Santa Monica is a trip down memory lane of our nation's history.

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Animated map of road tripEmma Kumer/rd.com

The Mother Road. America’s Highway. The Main Street of America. The Will Rogers Highway. Route 66 goes by many names, but no matter how travelers refer to it, there’s one constant everyone can agree on:

“Historic Route 66 is the quintessential American experience,” explains Ken Busby, executive director and CEO of Route 66 Alliance, a nonprofit organization in Tulsa, Oklahoma dedicated to the Route’s preservation, promotion and enhancement. “It speaks to westward migration during the Great Depression, a road of hopes and dreams and opportunities. Route 66 also represents the entrepreneurial spirit of America—from diners and motels to curio shops and roadside attractions, there is always something to see and do. Route 66 is the most iconic highway in the world, known by people from all four corners of the earth.” This popular 2,448-mile journey between Chicago and Santa Monica is a rite of passage for every road-tripper—as are these other best road trips in the United States.

Of course, as with most road trips, Route 66 is more about the journey than the destination. Aside from the 13 must-see sights you can only see on Route 66, there’s another aspect that keeps regulars coming back for more.

“It’s not the road and it’s not the attractions—it’s the people,” says Jim Conkle, CEO of Mother Road Enterprises who’s traveled Route 66 more than 200 times since his first trip in 1949. “The people are from all walks of life, from every country in the world. It’s really a smorgasbord of cultures and languages. If you travel Route 66 and don’t immerse yourself with the people, you’re missing the key to the whole experience. Be very open-minded, because you’re more than likely going to come away from any trip on Route 66 with a whole bunch of new friends.”

Fast facts

  • The moniker “The Mother Road,” was coined by John Steinbeck in his 1939 Pulitzer Prize-winning book The Grapes of Wrath, a tale of an Oklahoman family traveling Route 66 to start a new life in California during the Great Depression.
  • In 1946, Nat King Cole recorded “(Get Your Kicks on) Route 66” — the lyrics, written by songwriter Bobby Troup during his family’s own cross-country adventure, follow the path of the route from Chicago to Los Angeles.
  • Based on numbers collected by the state Route 66 associations and the National Travel and Tourism Office, approximately 2 to 3 million travelers from across the United States and around the world make some portion of Route 66 a destination each year.
  • As part of a major national marketing campaign in 1952, historic Route 66 was dubbed the Will Rogers Highway to celebrate the famous stage and motion picture actor, cowboy, humorist, and social commentator from Oklahoma.
  • Pixar’s 2006 animated film Cars was set in the fictional town of Radiator Springs, based on several small towns between Oklahoma and Arizona along Route 66. Author and historian Michael Wallis, founder of the Route 66 Alliance, lent his voice to the role of the Sheriff in the movie. Discover the iconic movie set in your state.

Route 66 history

Drone view of American car driving in a straight road of the famous Route 66.Artur Debat/Getty Images

  • Route 66 was anointed on November 11, 1926, but it would take until 1938 before the entire route was paved with concrete. It quickly became one of the nation’s principal east-west routes, not only connecting small rural towns to each other but also connecting Chicago to Los Angeles via the nation’s first all-weather road. By comparison, the country’s first transcontinental road for automobiles—Lincoln Highway, which was dedicated in 1913 and runs on a more northerly route—became impassable during wet weather conditions, making year-round travel impossible.
  • According to the National Historic Route 66 Federation, an estimated 210,000 people migrated to California to escape the Dust Bowl during the 1930s—for them, Route 66 symbolized a road to opportunity as they left their drought-ruined farms behind and looked for work out west.
  • When President Eisenhower signed the Federal-Aid Highway Act of 1956, which established America’s Interstate Highway System, Route 66 became obsolete. Interstates replaced large segments of the route, and the roadway was decommissioned in 1985.
  • Although the Route has undergone many realignments over the decades, the terminus points (roughly Chicago’s Navy Pier and the Santa Monica Pier) have remained largely unchanged. And with 85 percent of the original Route 66 still drivable today, it continues to provide travelers a scenic way to explore the Midwest, Great Plains, and Southwest.
  • No matter where you start or end your Route 66 road trip (some people go east to west to mimic the migration, others west to east, or you can pick a state or two to focus on), take ample time to enjoy the drive—plan 14 to 21 days for a leisurely end-to-end trip. “Do it in stretches and sections,” suggests Conkle. “Don’t be in a hurry. And you don’t necessarily have to set motel reservations up ahead of time, because you don’t know where you’ll end up each day. The hardest part of traveling Route 66 is not getting someplace, it’s leaving someplace. I like to tell people there are nine states on Route 66: The eight geographic states, and the biggest state of all—the state of mind.” Before you start your trip, brush up on these 15 essential road trip planning tips.

Illinois

Route distance: 300 miles

Suggested length of time: 2 to 3 days

Illinois is home to a 300-mile stretch of The Mother Road. The official “Begin Route 66” sign is in downtown Chicago, on the northwest corner of Adams St. and Michigan Avenue (across from the Art Institute of Chicago). If you’re doing the trip in reverse, the “End Route 66” is one block south, on Michigan and Jackson. Begin with a pre-trip stay at the Palmer House a Hilton Hotel to ensure you’re well-rested for the road—this historic hotel just steps from the start of Route 66 is the longest-continually operating hotel in North America, and boasts an opulent, frescoed lobby.

One notable stop heading southwest is the Illinois Route 66 Hall of Fame and Museum in Pontiac, which is filled with interesting memorabilia, including a photo op with the world’s largest Route 66 shield mural, (one of the 10 must-stop attractions for the best Route 66 road trip. Continuing on, stop in Wilmington at The Launching Pad, a historic Route 66 diner where you can take a selfie with Gemini Giant, a 30-foot tall statue named after the Gemini Space Program. Be sure to work up an appetite heading into Springfield, because the Cozy Dog Drive-In is still serving up the same batter recipe on their Cozy Dogs (aka, corn dogs) that was created back in 1946 and introduced at the Illinois State Fair that same year. “This is where the hot dog on a stick was invented,” says Conkle. Spend the night in Springfield, at the Route 66 Hotel & Conference Center, and look for the Route 66 touches throughout the property.

The Ariston Café in Litchfield is coming up next—this family-owned restaurant opened its doors in 1924 (though it moved to this location in 1935) and is one of the oldest continually operational Route 66 restaurants. Henry’s Rabbit Ranch in Staunton is worth a stop and filled with historic vehicles, road memorabilia, and a replica of a Route 66 gas station. Finally, as you head out of Illinois, visit the Chain of Rocks Bridge. Completed in 1929, the one-mile-long bridge spans the Mississippi River on the north edge of St. Louis, Missouri—today, it’s open to pedestrians and bicycles and it’s also part of the Great River Road Trip.

Missouri

Old Chain of Rocks Bridgemarekuliasz/Getty Images

Route distance: 300 miles

Suggested length of time: 2 to 3 days

To enter Missouri, you’ll cross over the Mississippi River via the Old Chain of Rocks Bridge (shown above). Now that you’re in the Show-Me State, Busby promises another 300 miles of great sights as you continue southwest. Start at the Gateway Arch, which is actually an optical illusion) and grab a treat at the Ted Drewes Frozen Custard on Chippewa, located on historic Route 66 since 1941. Next up, grab your camera and head to Cuba, known as Route 66’s Mural City, these colorful community art pieces tell stories of war, industry, politics, and life along Route 66. If you’d like to stay in town overnight, choose the Wagon Wheel Motel, which is the oldest continuously operating motel on the route.

Have you always wanted to see the World’s Second-Largest Rocking Chair? Then make a beeline for Fanning. You won’t be able to climb up 56 feet onto the seat to see the strangest roadside attraction in the state, but standing in front of it makes for a great photo, too. Next, continue to Lebanon. “Plan on spending a night or two at the Munger Moss Motel,” says Busby. “It’s one of the few remaining mom and pop motels still operating on Route 66. It was built in 1946 but has been updated with modern amenities. This classic auto court welcomes you with themed rooms.”

Next, it’s on to Springfield, the official birthplace of Route 66. Why? Because it was named “U.S. 66,” via telegram at a meeting of highway officials in Springfield, Missouri on April 30, 1926. If you time your trip just right, you (and 75,000 other Route 66 enthusiasts) can visit during the annual Birthplace of Route 66 Festival. Springfield is also home to three sites on the National Register of Historic Places that are each worth a visit: Gillioz Theatre, a historic theatre that opened in 1926; Rock Fountain Court, a classic motor court developed in the mid-1940s; and the Abou Ben Adhem Shrine Mosque, a five-story building of arabesque design from 1923 that, for many years, was the site of the annual Shrine Circus. Spend the night in Springfield’s Best Western Route 66 Rail Haven, which is chockfull of nostalgia from its heyday. there’s even an Elvis suite with a jetted tub. Finally, finish the Springfield portion of your adventure at the Route 66 Car Museum to enjoy a collection of Brass Era, classics, sports, and celebrity vehicles (including the famous truck from the movie Grapes of Wrath starring Henry Fonda).

Kansas

Route distance: 13.2 miles

Suggested length of time: 1 day

Yes, the amount of Route 66 you’ll travel through Kansas is about equal to a half-marathon, so this leg will go quickly, but there are still a few noteworthy things to see through its three charming towns: Baxter Springs, Galena, and Riverton.

Just north of Baxter Springs and two miles west of Riverton is the picturesque Rainbow Bridge, which Busby says is the only remaining arch bridge of this type on Route 66. The Baxter Spring Heritage Center and Museum gives you some great history of the area and of course Route 66. In Riverton, stop by one of 25 old-fashioned general stores across America: the Williams’ Store (now Eisler Brothers Old Riverton Store). Opened in 1925, it’s the oldest continuously operating store on Route 66.

Finally, heading on to Galena before you enter Oklahoma, a must-stop is Cars on the Route, a gift shop housed in a former KanOtex Service Station. “Next to the station is Tow Tater, a 1951 International Boom truck that was the inspiration for ‘Tow Mater’ in the movie Cars, plus other vehicles that resemble some of the memorable characters from that film,” says Busby.

Oklahoma

Cyrus Avery Centennial PlazaMark Williamson/Getty Images

Route distance: 410 miles

Suggested length of time: 2 to 3 days

Now that you’ve traveled the shortest stretch of Route 66, it’s time for the longest stretch of the original road (today, Arizona has the longest stretch of historic Route 66). Busby recommends beginning with a stop at the Coleman Theatre in Miami, a fully restored Spanish Colonial Mission-style theatre built in 1929 featuring opulent Louis XV décor and a “Mighty Wurlitzer” pipe organ.

Next is the town of Vinita, and plan for breakfast or lunch at Clanton’s Café, which has been featured on Food Network’s Diners, Drive-Ins, and Dives and known for its world-famous calf fries (yep, deep-fried calf testicles). If that doesn’t sound too appetizing, have some of these healthy road trip snacks on hand as back up. Continuing on, visit Totem Pole Park near Chelsea, and marvel at the world’s largest concrete totem pole, which stands 60 feet high. There’s also the Will Rogers Memorial Museum and Birthplace Ranch in Claremore, as well as the Blue Whale of Catoosa, a waterfront structure you can walk inside or picnic nearby.

In Tulsa, be sure and stop by Cyrus Avery Centennial Plaza (shown above). “Here, you can learn more about the history of the “Father of Route 66,” says Busby, explaining that Cyrus Avery was responsible for convincing the Joint Board on Interstate Highways that Route 66 should go through Tulsa because of the city’s concrete and steel-reinforced bridge that crosses the Arkansas River. If you’re looking for a place to spend the night, the fully restored Campbell Hotel is a great choice—built in 1927, it was the first hotel on Route 66 in Oklahoma. With themed rooms, including a Route 66 Room, an Art Deco Room, and a mid-century modern Lunar Eclipse Room, you’ll enjoy every detail.

No trip to Oklahoma would be complete without a meal at the Rock Café in Stroud, with an internationally themed menu.

Further west, in Arcadia, you’ll find the landmark tourist attraction Arcadia Round Barn (built by a local farmer in 1898) and Pops, which offers a signature collection of 700 kinds of soda, sparkling waters, and hand-dipped ice cream milkshakes.

The Oklahoma Route 66 Museum in Clinton includes nostalgic experiences, including a 1950s diner, sounds of the Big Band era, and various exhibits on the Route 66 experience. Discover the strangest museum in your state.

Texas

Route distance: 200 miles

Suggested length of time: 1 to 2 days

Texas may be the second-largest state in America, so you may find it surprising that it’s hosts the second-shortest stretch of historic Route 66. You’ll be driving through the panhandle, beginning with the city of Shamrock. Here, you’ll find the U-Drop Inn, an Art Deco building built in 1936 that originally housed a gas station and café (the distinctive design was featured in Cars, as the inspiration for Ramone’s House of Body Art).

Since everything’s bigger in Texas, save your appetite for a memorable meal at The Big Texan Steak Ranch & Brewery. This is the home of the 72-oz. steak challenge, if you can eat the entire 4.5-pound steak plus sides in an hour, it’s free!

Continuing west, you will find one of the most iconic stops on Route 66: Cadillac Ranch, in Amarillo. One of the real-life locations that inspired popular Disney attractions, this roadside sculpture consists of ten vintage Cadillacs buried nose-down, up to their windshields at the same angle as that of the Great Pyramid of Giza in Egypt.

Once you reach Adrian, you’ve made it to the midpoint between Chicago and Los Angeles. Celebrate completing the first half of your journey by standing on the halfway line at Midpoint Café and Gift Shop and enjoying a piece of their famous pecan cobbler. You’ve completed 1,139 miles and have 1,139 more to go!

 

New Mexico

Street scne with decorative lighing Gallup New Mexico Route 66.brians101/Getty Images

Route distance: 400 miles

Suggested length of time: 2 to 3 days

“The Land of Enchantment is just that for Route 66 travelers, offering almost 400 miles of history to explore,” says Busby. Plan to spend at least one day and night in Tucumcari—this town is full of active restaurants and motels on Route 66, built in the 1930s, 1940s, and 1950s. The most notable? The Blue Swallow Motel, a classic motor court that has been serving Route 66 travelers since 1939.

Carve out some time to spend in Santa Rosa, too. One popular attraction is the Route 66 Auto Museum, which draws car buffs from across the country and beyond. The museum houses a large collection of classics, low riders, muscle cars and motorcycles, plus, gas pumps, and other auto memorabilia from the early days of Route 66. Also, check out the crystal-blue natural swimming hole with hidden caves: Blue Hole. You might not have remembered to pack your SCUBA gear on your Route 66 road trip, but believe it or not, this is one of the most popular dive destinations in the country and one of the best natural swimming pools in the United States.

“You will want to take the original 1926 alignment of Route 66 so that you will travel through Santa Fe,” recommends Busby. “A night at the La Fonda on the Plaza hotel is a must, as is a visit to the Cathedral Basilica of St. Francis of Assisi.”

Heading on to Albuquerque, you will be welcomed by all of the neon signs on Central Avenue (Route 66). Stop at the 66 Diner for a burger and shake or its trademark Pile Up, a breakfast scramble that includes everything but the kitchen sink.

Your last major stop in New Mexico will be Gallup. It’s one of 12 small towns with beautiful architecture and the buildings along Route 66 in the stretch between Puerco Street and 4th Street are almost all original: The Santa Fe Station (now the Gallup Cultural Center, which includes a museum dedicated to American Indian culture), Kitchens Opera House (in the block between 2nd and 3rd on route 66), Richardsons Trading Post (established in 1938), and the Rex Museum.

Have dinner and spend the night at El Rancho Hotel and Restaurant, during its heyday, John Wayne, Katharine Hepburn, Humphrey Bogart, Ronald Reagan, and Kirk Douglas all stayed here when making Hollywood movies.

Arizona

Route distance: 250 miles

Suggested length of time: 2 to 3 days

Route 66 enters the state in Lupton (on the border of New Mexico) and continues for 250 miles across the northern half of Arizona—passing through Holbrook, Winslow, Flagstaff, Williams, Seligman, Kingman, Oatman, and finally Topock before the final leg into California.

Besides seeing the Petrified Forest National Park, which is the only national park on Route 66 (check out the 15 best national park road trips to see more of America’s many wonders), you can spend a night in a teepee at Holbrook’s Wigwam Motel.

The next day, head to Winslow. Be sure and stop by Standin’ on the Corner Park, which commemorates the song “Take It Easy”—a monument was built to acknowledge the Jackson Browne and Glenn Frey tune made famous by the Eagles. Spend the night at Winslow’s famous La Posada Hotel and have dinner in the Turquoise Room.

Less than 20 miles west is Meteor Crater and Barringer Space Museum, revered as the world’s best-preserved meteor impact site. Drive another 35 miles west to Flagstaff, home of the world’s largest contiguous Ponderosa Pine forest. Here, you can touch and feel the pure fabric of Route 66—about 900-feet of untouched Mother Road (original Portland cement surface) that has been adopted into the Flagstaff Urban Trails System. There are signs and picnic tables, so you can spend a little time with the old highway in the shadow of Mt. Elden.

Moving on to Williams—the last town on Route 66 to be bypassed by Interstate 40 in 1986—you’ll find a haven for neon lovers. Plus, many of the buildings along Route 66 in Williams were constructed in the late 1800s. Spend a night at the Red Garter Inn and Bakery, a beautifully resorted 1897 saloon and bordello that captures the 1890’s old western atmosphere thanks to its two-story Victorian Romanesque architecture and antique furnishings.

Like other towns along Route 66, Seligman is a place you do not want to rush through. Stop by Angel Delgadillo’s Route 66 Gift Shop and Visitor Center and pick up a Walking Tour Guide to Historic Seligman. This 20-minute walking tour guides you through the original center of Seligman, sharing the colorful history of this once-thriving railroad town and it’s a great place to find the perfect souvenir. Your upcoming drive from Seligman to Oatman puts you on the longest stretch of original Route 66 road of your entire journey.

In Kingman, visit Giganticus Headicus, a 14-foot-tall Tiki-style head at Antares Visitor Center, situated along the longest continuous curve on a U.S. highway (approximately 2 miles long). From here, it’s on to Oatman, a former mining town located in the Black Mountains of Mohave County that was all but abandoned by the 1960s after the gold mines closed in the 1940s. Wild burros (donkeys) freely roam the town. If you visit on a weekend, there’s a good chance you’ll see a classic car rally or mock “Wild West” shootouts right down the middle of old 66.

Your last stop is Topock on the California-Arizona border—the Old Trails Bridge that crosses the Colorado River here was featured in the opening credits of the movie Easy Rider.

California

The Historic Route 66 SignSupannee_Hickman/Getty Images

Route distance: 315 miles

Suggested length of time: 2 to 3 days

Welcome to the final leg of your journey. “In the heart of the California desert, you will find Elmer’s Bottle Tree Ranch just south of Helendale,” says Busby. “It’s literally a ranch of artistic metal pipes with bottles hanging from them.”

A stop at the Route 66 Mother Road Museum in Barstow provides a good history of Route 66 and the Mojave Desert communities. And an overnight stay in San Bernadino offers two iconic stops: the first McDonald’s restaurant, which is now the First Original McDonald’s Museum (here’s what McDonald’s looked like when it first opened in 1955) and the Wigwam Motel, one of the few remaining wigwam motels in the country.

You’ll then take Route 66 through Rancho Cucamonga before hopping on the 101 to Santa Monica Boulevard. Finally, arrive at the western terminus of Santa Monica Pier—a plaque dedicated to Will Rogers sits in a park on Santa Monica and Ocean Avenue, and a sign between Pacific Park and the Santa Monica Pier confirms it’s the “end of the trail” for your historic Route 66 road trip.

Ready to keep on rolling? Learn about another popular route: the Atlantic Coast road trip.

For more on where to go and what to see around the country, check out our Ultimate American Road Trip Guide.

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Jill Schildhouse
Jill Schildhouse is an award-winning writer based in Phoenix who regularly covers travel, health and wellness, personal finance and e-commerce. Her bylines have appeared in Reader's Digest, The Healthy, Oxygen, AAA, Brides, Vegetarian Times, and Phoenix Home & Garden magazines, among others. She earned a BA in corporate communications from Northern Illinois University. Follow her on Instagram, Twitter, Facebook and Linkedin